Thionyl Chloride → {4-[2-(4-Fluorophenyl)ethyl]piperazin-1-yl}quinolin-8-ylmethanone

HRID 2054695노트

반응식

HRID 2054695 반응식
S(Cl)(Cl)=O.[N:5]1[C:14]2[C:9](=[CH:10][CH:11]=[CH:12][C:13]=2[C:15]([OH:17])=O)[CH:8]=[CH:7][CH:6]=1.N1C2C(=CC=CC=2C(Cl)=O)C=CC=1.[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][N:40]2[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]2)=[CH:34][CH:33]=1>C1COCC1.ClCCl.CN(C1C=CN=CC=1)C.C(N(CC)CC)C>[F:31][C:32]1[CH:37]=[CH:36][C:35]([CH2:38][CH2:39][N:40]2[CH2:41][CH2:42][N:43]([C:15]([C:13]3[CH:12]=[CH:11][CH:10]=[C:9]4[C:14]=3[N:5]=[CH:6][CH:7]=[CH:8]4)=[O:17])[CH2:44][CH2:45]2)=[CH:34][CH:33]=1

참가 물질

9

반응물 4

HCID 24386Thionyl ChlorideHCID 665828-Quinolinecarboxylic acidHCID 112545221-(2-(4-Fluorophenyl)ethyl)piperazineHCID 14722777Quinoline-8-carbonyl chloride

생성물 1

HCID 10155608{4-[2-(4-Fluorophenyl)ethyl]piperazin-1-yl}quinolin-8-ylmethanone

시약·촉매·용매 4

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매HCID 8471Triethylamine용매

실험 절차

0.34 ml of thionyl chloride is added to a suspension of 0.4 g of quinoline-8-carboxylic acid in THF, and the mixture is refluxed for 1 hour. The mixture is then freed from solvent, and the residue (quinoline-8-carbonyl chloride) is taken up in 50 ml of dichloromethane. 2.1 g of polymeric DMAP (Aldrich, Article No. 35,998-2), 0.6 ml of triethylamine and 0.6 g of 1-[2-(4-fluoro-phenyl)ethyl]piperazine are added to this solution, and the mixture is stirred at room temperature for 5 days. Conventional work-up gives {4-[2-(4-fluorophenyl)ethyl]piperazin-1-yl}quinolin-8-ylmethanone.

후처리

  1. temperaturethe mixture is refluxed for 1 hour

출처 및 근거

ORD 기록
ord-520568b1c09d4ec98da56c7bd393648f
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07329749B2

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